40663-68-1

Basic information

• Product Name: 4-ALLYLOXYBENZALDEHYDE
• Synonyms: TIMTEC-BB SBB007994;P-ALLYLOXYBENZALDEHYDE;4-ALLYLOXYBENZALDEHYDE;AKOS BC-3068;ASISCHEM R34721;4-Allyloxybenzaldehyde,97%;4-ALLYOXYBENZALDEHYDE;4-Allyloxybenzaldehyde,98%
• CAS NO: 40663-68-1
• Molecular Formula: C₁₀H₁₀O₂
• Molecular Weight: 162.19
• EINECS: 255-027-2
• Product Categories: Aromatic Aldehydes & Derivatives (substituted);Aldehydes;C10 to C21;Carbonyl Compounds
• Mol File: 40663-68-1.mol

Chemical Properties

• Melting Point: 150-152℃ (18 TORR)
• Boiling Point: 150-152 °C18 mm Hg(lit.)
• Flash Point: >230 °F
• Appearance: Clear slightly yellow/Viscous Liquid
• Density: 1.058 g/mL at 25 °C(lit.)
• Vapor Pressure: 0.00366mmHg at 25°C
• Refractive Index: n20/D 1.568(lit.)
• Water Solubility: Immiscible in water.
• Sensitive: Air Sensitive
• BRN: 2206924
• CAS DataBase Reference: 4-ALLYLOXYBENZALDEHYDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-ALLYLOXYBENZALDEHYDE(40663-68-1)
• EPA Substance Registry System: 4-ALLYLOXYBENZALDEHYDE(40663-68-1)

Safety Data

• Hazard Codes: Xi
• Statements: 43-36/38
• Safety Statements: 36/37-37/39-26
• WGK Germany: 3
• HazardClass: IRRITANT
• Hazardous Substances Data: 40663-68-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
4-Allyloxybenzaldehyde is used as a pharmaceutical intermediate, playing a crucial role in the synthesis of various drugs and medications. Its chemical properties make it a valuable component in the development of new pharmaceutical products.
Used in Chemical Synthesis:
4-Allyloxybenzaldehyde may be used in the preparation of several compounds, such as:
1. 4,6,4′,6′-O-di-4-allyloxybenzylidene-α,α-D-trehalose: 4-ALLYLOXYBENZALDEHYDE is synthesized using 4-allyloxybenzaldehyde and has potential applications in various fields.
2. 3-allyl-4-hydroxybenzaldehyde: Another compound derived from 4-allyloxybenzaldehyde, which can be utilized in the development of new chemical products.
3. (±)-4-allyloxymethamphetamine (ALLMA): 4-ALLYLOXYBENZALDEHYDE is also synthesized using 4-allyloxybenzaldehyde and has potential applications in the pharmaceutical and chemical industries.

InChI:InChI=1/C10H10O2/c1-2-7-12-10-5-3-9(8-11)4-6-10/h2-6,8H,1,7H2

Upstream product

• 123-08-0 4-hydroxy-benzaldehyde 
• 106-95-6 allyl bromide 
• 107-05-1 3-chloroprop-1-ene 
• 556-56-9 allyl iodid 
• 22666-84-8 4-hydroxybenzaldehyde sodium salt 
• 107-18-6 allyl alcohol 
• 74323-90-3 para-(allyloxy)benzaldehyde dimethylacetal 
• 3256-45-9 4-allyloxybenzyl alcohol 
• 123-11-5 4-methoxy-benzaldehyde 
• 109-64-8 1,3-dibromo-propane 
• 90-02-8 salicylaldehyde 
• 1202354-77-5 C₁₈H₁₉NO₂ 
• 36844-51-6 4-allyloxybenzoyl chloride 
• 106-41-2 4-bromo-phenol 

Downstream Products

• 101285-05-6 isonicotinic acid-(4-allyloxy-benzylidenehydrazide) 
• 41052-88-4 4-hydroxy-3-(2-propen-1-yl)benzaldehyde 
• 50615-92-4 (4-allyloxy-benzyliden)-aniline 
• 115760-28-6 bis-(4-allyloxy-benzylidene)-benzidine 
• 34209-93-3 trans-4-Allyloxy-β-nitrostyrol 
• 3256-45-9 4-allyloxybenzyl alcohol 
• 64518-76-9 4-(4-Allyloxy-benzylamino)-benzoic acid 
• 64518-77-0 4-(4-Allyloxy-benzylamino)-benzoic acid ethyl ester 
• 80304-92-3 (E)-4-(4-Allyloxy-phenyl)-1-morpholin-4-yl-but-3-en-2-one 
• 106456-81-9 meso-tetrakis<4-(allyloxy)phenyl>porphyrin 
• 153225-88-8 2-hydroxy-2-<4-(2-propenyloxy)phenyl>acetonitrile 
• 210779-18-3 1-Allyloxy-4-(2,2-dibromo-vinyl)-benzene 
• 700-58-3 2-Adamantanone 
• 127872-11-1 N-<(4-<(prop-2-enyl)oxy>phenyl)methylidene>methylamine N-oxide 

Relevant articles and documents

Total Syntheses of Prenylated Isoflavones from Erythrina sacleuxii and Their Antibacterial Activity: 5-Deoxy-3′-prenylbiochanin A and Erysubin F

The prenylated isoflavones 5-deoxyprenylbiochanin A (7-hydroxy-4′-methoxy-3′-prenylisoflavone) and erysubin F (7,4′-dihydroxy-8,3′-diprenylisoflavone) were synthesized for the first time, starting from mono- or di-O-allylated chalcones, and the structure of 5-deoxy-3′-prenylbiochanin A was corroborated by single-crystal X-ray diffraction analysis. Flavanones are key intermediates in the synthesis. Their reaction with hypervalent iodine reagents affords isoflavones via a 2,3-oxidative rearrangement and the corresponding flavone isomers via 2,3-dehydrogenation. This enabled a synthesis of 7,4′-dihydroxy-8,3′-diprenylflavone, a non-natural regioisomer of erysubin F. Erysubin F (8), 7,4′-dihydroxy-8,3′-diprenylflavone (27), and 5-deoxy-3′-prenylbiochanin A (7) were tested against three bacterial strains and one fungal pathogen. All three compounds are inactive against Salmonella enterica subsp. enterica (NCTC 13349), Escherichia coli (ATCC 25922), and Candida albicans (ATCC 90028), with MIC values greater than 80.0 μM. The diprenylated natural product erysubin F (8) and its flavone isomer 7,4′-dihydroxy-8,3′-diprenylflavone (27) show in vitro activity against methicillin-resistant Staphylococcus aureus (MRSA, ATCC 43300) at MIC values of 15.4 and 20.5 μM, respectively. In contrast, the monoprenylated 5-deoxy-3′-prenylbiochanin A (7) is inactive against this MRSA strain.

Nickel Hydride Catalyzed Cleavage of Allyl Ethers Induced by Isomerization

This report discloses the deallylation of O - and N -allyl functional groups by using a combination of a Ni-H precatalyst and excess Bronsted acid. Key steps are the isomerization of the O - or N -allyl group through Ni-catalyzed double-bond migration followed by Bronsted acid induced O/N-C bond hydrolysis. A variety of functional groups are tolerated in this protocol, highlighting its synthetic value.

Reaction-based fluorescent silk probes with high sensitivity and selectivity to Hg2+and Ag+ions

The detection and removal of heavy metals in the environment is urgent and meaningful. In this work, two types of fluorescent functionalized silksOSPandASPhave been prepared using worm silk as the substrate. These fluorescent silk probes exhibit an obvious fluorescence quenching effect in the presence of Hg2+or Ag+, enabling silk to specifically detect Hg2+or Ag+. An obvious color response occurs under visible light, from yellow to brown or gray, thereby realizing dual-channel identification of fluorescence and colorimetry. In addition, its sensing mechanism has been studied, and it is found that the probe reacts with metal ions as a reactive response. Compared with the fluorescent probes bearing one C-C/C-C bond, the probes with two terminal C-C/C-C bonds are more sensitive. And the excellent recognition ability can make the limit of detection as low as 0.25 μM. This indicates that silk fluorescent probes can be used to detect Hg2+and/or Ag+

Allylphenols as a new class of human 15-lipoxygenase-1 inhibitors

In this study, a series of mono- and diallylphenol derivative were designed, synthesized, and evaluated as potential human 15-lipoxygenase-1 (15-hLOX-1) inhibitors. Radical scavenging potency of the synthetic allylphenol derivatives was assessed and the results were in accordance with lipoxygenase (LOX) inhibition potency. It was found that the electronic natures of allyl moiety and para substituents play the main role in radical scavenging activity and subsequently LOX inhibition potency of the synthetic inhibitors. Among the synthetic compounds, 2,6-diallyl-4-(hexyloxy)phenol (42) and 2,6-diallyl-4-aminophenol (47) showed the best results for LOX inhibition (IC50 = 0.88 and 0.80 μM, respectively).

Iodine-DMSO catalyzed chemoselective oxidative aromatization and deallylation, nondeallylation of aryl allyl ether of tetrahydro-β-carboline

We have developed a simple method for the chemoselective aromatization of tetrahydro-β-carboline with selective nondeallylation O-allyl groups in the presence of iodine (100 mol %) in dimethyl sulfoxide/H2O2. A convergent approach toward the oxidative aromatization with selective deallylation (deprotection) of O-allyl-tetrahydro-β-carboline using iodine in dimethyl sulfoxide/HCl has been described. The present protocol contains cheap catalyst, easy work up, normal reaction conditions, and high selectivity.

Introducing the Tishchenko reaction into sustainable polymer chemistry

Taking advantage of the structural characteristics of lignin-derived phenolic compounds, a combination of the Williamson and Tishchenko reactions produced a series of new α,ω-diene functionalized carboxylic ester monomers from both petrochemical and renewable resources, which were applicable in subsequent thiol-ene click and acyclic diene metathesis (ADMET) polymerizations, providing a series of poly(thioether esters) and unsaturated aromatic-aliphatic polyesters with high molecular weights.

Enantioselective Synthesis of 3-Fluorochromanes via Iodine(I)/Iodine(III) Catalysis

The chromane nucleus is common to a plenum of bioactive small molecules where it is frequently oxidized at position 3. Motivated by the importance of this position in conferring efficacy, and the prominence of bioisosterism in drug discovery, an iodine(I)/iodine(III) catalysis strategy to access enantioenriched 3-fluorochromanes is disclosed (up to 7:93 e.r.). In situ generation of ArIF2 enables the direct fluorocyclization of allyl phenyl ethers to generate novel scaffolds that manifest the stereoelectronic gauche effect. Mechanistic interrogation using deuterated probes confirms a stereospecific process consistent with a type IIinv pathway.

Nitrile Synthesis by Aerobic Oxidation of Primary Amines and in situ Generated Imines from Aldehydes and Ammonium Salt with Grubbs Catalyst

Herein, a Grubbs-catalyzed route for the synthesis of nitriles via the aerobic oxidation of primary amines is reported. This reaction accommodates a variety of substrates, including simple primary amines, sterically hindered β,β-disubstituted amines, allylamine, benzylamines, and α-amino esters. Reaction compatibility with various functionalities is also noted, particularly with alkenes, alkynes, halogens, esters, silyl ethers, and free hydroxyl groups. The nitriles were also synthesized via the oxidation of imines generated from aldehydes and NH4OAc in situ. (Figure presented.).

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Ancillary ligands switch the activity of Ru–NHC-based oxidation precatalysts

Herein we demonstrate how the inner-sphere coordinating ligands switch the activity of Ru–NHC-based oxidation precatalysts in the oxidative conversion of olefins to carbonyl compounds, with the help of a series of systematically varied imidazolydene-NHC (Im-NHC) and triazolydene-NHC (Tz-NHC)-based ruthenium(II)-complexes. It is shown that the catalytic activity of the para-cymene-containing precatalysts varies in the order of [(Tz-NHC)Ru(para-cymene)Cl]+ > [(Im-NHC)Ru(para-cymene)Cl]+, while the order of activity of the MeCN-containing precatalysts is found to be reversed, i.e., [(Im-NHC)Ru(MeCN)4]2+ > [(Tz-NHC)Ru(MeCN)4]2+. Along with the electronic influence of the NHC ligands, the effect of the lability of the para-cymene and MeCN ligands, and the overall charge of the complexes might be attributed toward such a switching of catalytic activity. This finding led to develop a new precatalyst with improved activity which was further utilized in selective oxidation of a series of styrene substrates containing other oxidation-sensitive functionalities.